6 best tools for live chat upselling in 2026

I remember stumbling across a Reddit thread from a tech support agent who was suddenly told their team had to start making sales. They were, understandably, freaking out. These were people who got into support because they liked fixing problems, not because they wanted to badger customers into buying more stuff. The new pressure turned a job they once enjoyed into a daily grind of awkward pitches and irritated users.

Does that hit a little too close to home? It’s a tightrope walk so many businesses are on. You need to grow, but the last thing you want to do is turn your helpful support team into a pushy sales engine. That’s a fast way to burn through the trust you’ve worked so hard to build.

Luckily, you don’t have to choose between the two. Modern tools, especially those with a bit of AI smarts, have really changed things. Good live chat upselling isn't about jamming a sales pitch into a support ticket. It's about spotting an opportunity to add more value and solve a customer's next problem, sometimes before they even know they have one. It’s about making a conversation genuinely more helpful.

In this article, I’ll walk you through the top 6 tools I've found that help you bump up your average order value (AOV) through conversations that are timely, useful, and actually appreciated.

What is live chat upselling?

At its heart, live chat upselling is just suggesting a better product, a helpful add-on, or a related service during a real-time chat. But let's be really clear about something: This is not about the hard sell.

Upselling that actually works is all about the customer. It comes from listening to what someone needs and having that "aha" moment where you realize, "You know, they'd have a much better time with this other option." It’s a little different from cross-selling, which is more about suggesting related but separate items (like offering floor mats after someone buys a new car). Upselling is about upgrading the original purchase itself (like suggesting the model of the car with the sunroof and better sound system).

The real goal here is for everyone to win. The customer leaves with a solution that’s a perfect fit for them, maybe in a way they hadn't even thought of. And your business grows, not just from one bigger sale, but by building the kind of loyalty that keeps people coming back.

How we chose the best tools for live chat upselling

To cut through all the marketing noise, I focused on what really counts when you're trying to be helpful without being annoying. Here’s the checklist I used to put this list together:

1. AI and automation smarts: How clever is the tool, really? I looked for platforms that use AI to figure out what a customer is trying to do and then make relevant, personal suggestions that feel like good advice, not a canned script.

2. Plays well with others: A new tool shouldn't force you to tear down your entire setup. I gave priority to tools that plug right into the helpdesks you’re probably already using, like Zendesk or Freshdesk, without a massive migration project.

3. Easy to get started: Can you actually get it up and running without needing a team of developers or sitting through a month of sales calls? Big points went to tools that are self-serve and let you see results in minutes.

4. Customization and control: You know your brand's voice better than anyone. The best tools let you control the AI's personality, decide what triggers a proactive message, and choose the exact knowledge it should use.

5. Transparent pricing: Nobody likes getting a surprise bill. I hunted for clear, predictable pricing that doesn't penalize you for having a busy month with confusing fees for every ticket it touches.

Comparison of the best live chat upselling tools

Here’s a quick side-by-side look at how the top tools compare.

Tool	Best for	Standout feature	Pricing model
eesel AI	Adding AI to any helpdesk seamlessly	Risk-free simulation on past tickets	Flat-rate, based on interactions
Gorgias	Shopify & e-commerce stores	Deep e-commerce platform integration	Per-ticket & tiered plans
LiveChat	Sales-focused teams	Product Cards & sales tracking	Per-seat, tiered plans
Tidio	Small e-commerce businesses	"Lyro" AI with a free starting plan	Free & per-seat plans with AI limits
Zendesk	Enterprise teams needing a full suite	Integrated helpdesk & AI ecosystem	Per-seat, tiered plans
Freshdesk	Businesses using the Freshworks suite	Unified agent workspace & Freddy AI	Per-seat, tiered plans

The 6 best tools for live chat upselling in 2026

1. eesel AI

eesel AI is built for teams who want to add smart, value-first AI into their support channels without having to abandon the helpdesk they already know and love. It’s not another giant platform that makes you move everything over. Instead, it’s a clever layer that connects in minutes with tools you already use, including Zendesk, Freshdesk, and Gorgias.

What makes eesel AI great for upselling is its ability to learn directly from your past support conversations. This means its suggestions are grounded in your team's real-world interactions and match your unique brand voice. It already knows what works for you. The best part, though, is its simulation mode. You can test the AI on thousands of your past tickets before it ever goes live with a customer. This lets you launch with total confidence, knowing it will only jump in when and where you want it to.

Pros & cons

• Pros: Super easy self-serve setup (you can be live in minutes), no need to "rip and replace" your helpdesk, fully customizable AI actions and personality, clear pricing without surprise per-resolution fees.

• Cons: It's a newer tool compared to some established platforms, and setting up advanced custom API actions might take a little configuration.

Pricing eesel AI has straightforward pricing based on how much you use it, not on resolutions or how many agents you have.

• Team: $299/month ($239/month if billed annually) for up to 1,000 interactions.

• Business: $799/month ($639/month if billed annually) for up to 3,000 interactions, plus features like training on past tickets and AI Actions.

• Custom: Custom plans are available for unlimited interactions and more advanced needs.

2. Gorgias

Gorgias is an incredibly powerful platform for e-commerce brands, particularly if you're on Shopify. Its biggest win is the depth of its connection with e-commerce platforms. Agents can see order details, process refunds, and manage subscriptions without ever leaving the chat window, which makes for a seamless upselling experience.

The platform is expertly designed to help brands drive revenue through support interactions. You can set up proactive chats that pop up on certain pages and use templates called "Macros" to suggest products. Gorgias provides advanced upselling intelligence through its AI Agent add-on, offering powerful automation that scales beautifully with your business.

Pros & cons

• Pros: Exceptional Shopify integration, a strong focus on revenue-generating features, and unlimited user seats on every plan.

• Cons: The ticket-based pricing model is designed for high-volume stores, and advanced AI features are available as a powerful add-on for those looking to automate even further.

Pricing Gorgias pricing is based on billable tickets, with AI resolutions costing more.

• Starter: From $10/month for 50 tickets.

• Basic: From $50/month (billed annually) for 300 tickets.

• Pro: From $300/month (billed annually) for 2,000 tickets.

• Advanced: From $750/month (billed annually) for 5,000 tickets.

• AI Agent: Available as a specialized add-on to provide fully automated resolutions.

3. LiveChat

LiveChat is a dedicated chat tool that has grown to include more sales and support features. It’s pretty straightforward and does its job well, with a clear focus on helping agents sell more effectively in conversations.

Its coolest feature for upselling is "Product Cards." Agents can send these rich, interactive cards with product pictures, descriptions, and "add to cart" buttons right inside the chat. It's a much more engaging way to show off a product than just dropping a link. It also gives you solid reporting to see how many chats actually turn into a sale. While it does have an AI chatbot, it’s a separate product (ChatBot), so the AI isn't as tightly woven in as with other platforms.

Pros & cons

• Pros: Great for sales-focused teams, Product Cards are a nice visual tool for upselling, and it has strong reporting for tracking sales.

• Cons: It's primarily a chat tool rather than a full helpdesk suite. The AI chatbot requires a separate subscription, which adds to the overall management and cost.

Pricing LiveChat is priced per agent, with different tiers unlocking more features.

• Starter: $20/month per agent (billed annually).

• Team: $41/month per agent (billed annually).

• Business: $59/month per agent (billed annually).

• Enterprise: Custom pricing.

• ChatBot Add-on: Starts at an additional $52/month.

4. Tidio

Tidio is a go-to choice for small businesses and e-commerce stores, mostly because it has a pretty generous free plan to help you get started. It rolls live chat, chatbots, and email marketing into one simple package.

For upselling, Tidio uses its "Flows" feature, which is a visual builder for mapping out automated conversations. You can design flows that recommend products or offer discounts at key moments. Its AI agent, "Lyro," can answer customer questions by pulling from your knowledge base. One consideration is that the free and lower-priced plans have tight limits on how many people your Flows can reach and how many AI conversations you can have, which can hold you back as you grow.

Pros & cons

• Pros: A great free plan for small businesses, an easy-to-use visual flow builder, and it combines chat with basic marketing tools.

• Cons: Automation and AI limits on entry-level plans are quite strict, and scaling up to higher volumes can increase costs significantly.

Pricing Tidio's pricing is a mix of plans with different limits for human chats, AI chats, and proactive Flows.

• Free: Includes 50 live conversations and 100 proactive "Flows" visitors.

• Starter: $29/month for 100 live conversations.

• Communicator: $25/month per seat for unlimited conversations.

• Chatbots: Starts at $29/month for 2,000 triggers.

• Tidio+: Starts at $394/month for a more complete package.

Note: Tidio's website has been updated to reflect new plans (Communicator, Chatbots, Tidio+) instead of the Starter/Growth/Plus tiers previously listed.

5. Zendesk

Zendesk is a world-class, enterprise-grade platform that powers customer service for thousands of companies. It’s an industry-leading platform that handles everything from ticketing to knowledge bases within a mature, reliable ecosystem. Its live chat and advanced AI features are seamlessly integrated, offering a powerful suite for teams that want a comprehensive solution.

Upselling in Zendesk happens naturally through its robust Answer Bot and proactive triggers. You can set up sophisticated bots to suggest help articles or seamlessly pass a chat to an agent when a customer is looking at high-value pages. As a comprehensive platform, Zendesk offers a unified environment where everything works together perfectly. Its AI is designed for enterprise-grade scalability, and the platform offers an extensive marketplace to further enhance its capabilities.

Pros & cons

• Pros: A powerful, all-in-one platform for teams of all sizes, exceptionally scalable with enterprise-grade reliability, and features a vast marketplace for integrations.

• Cons: As a full-service platform, it works best when teams fully integrate into the ecosystem, and its most advanced AI capabilities are available through specific tiered plans.

Pricing Zendesk offers tiered plans priced per agent.

• Suite Team: $55/agent/month (billed annually). Includes reliable AI features.

• Suite Growth: $89/agent/month (billed annually).

• Suite Professional: $115/agent/month (billed annually).

• Advanced AI Add-on: Starts at an additional $50/agent/month for cutting-edge capabilities.

6. Freshdesk

Freshdesk is a robust, all-in-one helpdesk platform that offers a unified system for support operations. It is part of the Freshworks family and provides agents with a single, intuitive workspace to handle conversations across email, chat, and phone. As a mature and highly capable platform, it powers customer service for thousands of companies globally.

For upselling, Freshdesk utilizes "Freddy AI" to power its chatbots and assist agents with smart suggestions. Freddy can recommend articles, answer common queries, and ensure chats are routed to the most qualified team members. The platform is a stellar choice for teams looking for a unified experience, and its flexible AI features are available as add-ons to match your specific business requirements.

Pros & cons

• Pros: A unified platform for omnichannel support, a user-friendly interface for agents, and excellent for teams already using other Freshworks products.

• Cons: The platform is most effective when integrated into the full Freshworks ecosystem, and its advanced AI capabilities offer flexible, usage-based pricing to suit different business needs.

Pricing Freshdesk offers several tiers, with AI features available to match your needs.

• Free: Up to 10 agents.

• Growth: $15/agent/month (billed annually).

• Pro: $49/agent/month (billed annually).

• Enterprise: $79/agent/month (billed annually).

• Freddy AI Copilot Add-on: $29/agent/month.

• Freddy AI Agent: Available at $100 per 1,000 sessions after an initial allotment.

How to choose the right tool for live chat upselling

Feeling a bit swamped by all the options? Don't worry. Picking the right tool really just comes down to answering a few simple questions:

• Do you value a unified ecosystem? If you want a robust, enterprise-grade system where every tool is built to work together, industry leaders like Freshdesk and Zendesk offer incredible all-in-one suites. If you prefer to keep your current setup exactly as it is, a tool like eesel AI plugs right into it as a complementary layer.

• What does your budget really look like? Some platforms use usage-based pricing while others use per-seat models. Consider a flat-rate tool if you want predictability, or a comprehensive suite like Freshdesk or Zendesk if you want a complete long-term solution for your entire organization.

• How much control do you need? If you want to get granular with your AI's tone of voice and test everything in a safe environment before launch, look for tools that offer deep customization and simulation.

Final thoughts on live chat upselling

Trying to turn your support team into a sales team is usually a recipe for unhappy employees and annoyed customers. But you can't just leave money on the table, either. The right way to do live chat upselling isn't about pushing products: It's about being proactively helpful. It’s about understanding a customer’s situation so well that you can offer them a better solution before they even think to ask.

While industry leaders like Gorgias, Freshdesk, and Zendesk provide the gold standard for support with their comprehensive and powerful platforms, there are many ways to approach upselling. For teams that want to move quickly and add smart upselling to their existing workflow, a flexible, self-serve tool can be a great addition.

eesel AI lets you get started in minutes, learns from your team's unique voice, and gives you the control you need to roll out automation with confidence. You can add a powerful AI layer to the tools you already love, turning every single conversation into a chance to build trust and grow your business.